17643-36-6Relevant articles and documents
Improved synthesis of (Z,E)-9,11,13-tetradecatrienal, the sex pheromone of the Carob Moth Apomyelois (=Ectomyelois) ceratoniae (Lepidoptera: Pyralidae)
Noorbakhsh, Saeede,Alizadeh, Babak Heidary,Saber, Moosa,Farazmand, Hossein
, p. 199 - 201 (2017)
(Z,E)-9,11,13-Tetradecatrienal is a sex pheromone component emitted by virgin females of the Carob Moth Apomyelois ceratoniae Zeller (Lepidoptera: Pyralidae) which is an important pest of Iranian pomegranate fruits. Chemical control of this pest is not possible and biological methods with pheromones are used. The synthesis of the major component of the sex pheromone was achieved in fewer steps and with lower cost than previously. (Z,E)-9,11,13-Tetradecatrienal was synthesised by four steps with 59% overall yield. The coupling of a conjugated dienynol intermediate from E-1,2-dichloroethylene with vinyl magnesium bromide was achieved in good yield and followed by reduction of dienynol with activated zinc in THF-H2O and oxidation gave the aldehyde of the sex pheromone.
Structure based interference with insect behaviour - Cyclopropene analogues of pheromones containing Z-alkenes
Al Dulayymi, Juma'a R.,Baird, Mark S.,Simpson, Michael J.,Nyman, Susan,Port, Gordon R.
, p. 12509 - 12520 (1996)
Analogues of the pheromones of three insect species (Musca domestica L., Plutella xylostella L. and Ephestia elutella Hbn.) in which a Z-alkene has been replaced by a 1,2-disubstituted cyclopropene have been synthesized. The analogues interfere with normal mating behaviour for each species.
Synthesis of dansyl-labeled probe of thiophene analogue of annonaceous acetogenins for visualization of cell distribution and growth inhibitory activity toward human cancer cell lines
Kojima, Naoto,Suga, Yuki,Matsumoto, Takuya,Tanaka, Tetsuaki,Akatsuka, Akinobu,Yamori, Takao,Dan, Shingo,Iwasaki, Hiroki,Yamashita, Masayuki
, p. 1276 - 1283 (2015)
The convergent synthesis of the dansyl-labeled probe of the thiophene-3-carboxamide analogue of annonaceous acetogenins, which shows potent antitumor activity, was accomplished by two asymmetric alkynylations of the 2,5-diformyl THF equivalent with an alkyne having a thiophene moiety and another alkyne tagged with a dansyl group. The growth inhibitory profiles toward 39 human cancer cell lines revealed that the probe retained the biological function of its mother compound, and would be useful for studying cellular activity.
The synthesis and biological evaluation of a kabiramide C fragment modified with a WH2 consensus actin-binding motif as a potential disruptor of the actin cytoskeleton
Tetlow, Daniel J.,Winder, Steve J.,A?ssa, Christophe
, p. 807 - 810 (2016)
The F-actin depolymerisation potency of a fragment of kabiramide C was increased when modified with a WH2 consensus actin-binding motif LKKV. Despite its low affinity for actin monomers, a shorter analogous fragment not bearing LKKV was identified as a potent inhibitor of actin polymerisation and a promoter of its depolymerisation, resulting in a loss of actin stress fibres in cells.
Tetris in monolayers: Patterned self-assembly using side chain shape
Xue, Yi,Zimmt, Matthew B.
, p. 8832 - 8834 (2011)
The "kinked" shapes of conjugated alkadiynes constrain chain packing in monolayers on HOPG. Centrally located diyne units permit assembly of 1,5-bis(alkadiyne)anthracene monolayers. Off-center diynes inhibit self-assembly. Shape matched pairs of off-center diyne chains direct self-assembly of compositionally patterned, two component monolayers.
Stereodirectional synthesis of the main component of pheromone (9Z,12E)-tetradeca-9,12-dienyl acetate by cross-coupling
Matveeva,Erin,Leshcheva,Kurts
, p. 765 - 770 (2000)
By cross-coupling of alkynyl cuprate with crotyl halides was synthesized (9Z,12E)-tetradeca-9-12-dienyl acetate, the main component of pheromones of several insect species Lepidoptera. The assignment of the chemical shifts of diene system was performed by 1H and 13NMR spectroscopy.
Preparation method of furan macrocyclic compound, prepared furan macrocyclic compound and application of furan macrocyclic compound
-
, (2021/08/07)
The invention discloses a preparation method of a furan macrocyclic compound, the prepared furan macrocyclic compound and application of the furan macrocyclic compound. According to the preparation method disclosed by the invention, a macrocyclic alkyne olefine aldehyde compound is used as a raw material and is subjected to cyclization reaction under the catalysis of metal. The preparation method disclosed by the invention is simple to operate, simple and convenient in steps and high in efficiency, and the atom utilization rate is up to 100%. The reaction raw material macrocyclic alkyne olefine aldehyde compound can be obtained by a cyclic ketone compound or an alkyl alcohol compound through several steps of reaction with mature process and very high efficiency. The furan macrocyclic compound with a brand-new and special structure is obtained by the method, can be used as an element unit to synthesize a series of oligomerization furan compounds, and has potential optical application value.
Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides
Steib, Philip,Breit, Bernhard
, p. 6572 - 6576 (2018/05/08)
Herein, we report on the first enantioselective and atom-efficient catalytic one-step dimerization method to selectively transform ω-allenyl carboxylic acids into C2-symmetric 14- to 28-membered bismacrolactones (macrodiolides). This convenient asymmetric access serves as an attractive route towards multiple naturally occuring homodimeric macrocyclic scaffolds and demonstrates excellent efficiency to construct the complex, symmetric core structures. By utilizing a rhodium catalyst with a modified chiral cyclopentylidene-diop ligand, the desired diolides were obtained in good to high yields, high diastereoselectivity, and excellent enantioselectivity.
